Crystal structure of N -(4-hydroxybenzyl)acetone thiosemicarbazone

The structure of the title compound, C 11 H 15 N 3 OS, shows the flexibility due to the methylene group at the thioamide N atom in the side chain, resulting in the molecule being non-planar. The dihedral angle between the plane of the benzene ring and that defined by the atoms of the thiosemicarbazide arm is 79.847 (4)°. In the crystal, the donor–acceptor hydrogen-bond character of the –OH group dominates the intermolecular associations, acting as a donor in an O—H...S hydrogen bond, as well as being a double acceptor in a centrosymmetric cyclic bridging N—H...O,O′ interaction [graph set R 2 2 (4)]. The result is a one-dimensional duplex chain structure, extending along [111]. The usual N—H...S hydrogen-bonding association common in thiosemicarbazone crystal structures is not observed.